A person with horns.
Another person, standing up.
No, not that person. This person has a thin, narrow body.
No, not that one. This shape is a person with a pair of pointed ears.
No, not that one. A bowl with two pointed feet.
Correct. A small flag on a short pole.
Not the shape I meant, but a correct answer so keep it. A shape with a white cut out in the middle.
No, not that one. This shape has a hole in it.
Correct. A square with a pole to its right.

Outcome: successful
Speaker comments: Bot got a right answer off a wrong prompt, but I tried to tell it that and it seemed to listen. :)